73062-94-9Relevant academic research and scientific papers
Cycloadditions in Syntheses. XXXII. Intramolecular Photocycloaddition of 4-(ω-Alkenyloxy)quinolin-2(1H)-one: Synthesis of 2-Substituted Cyclobutaquinolin-3(4H)-ones
Kaneko, Chikara,Suzuki, Takeshi,Sato, Masayuki,Naito, Toshihiko
, p. 112 - 123 (2007/10/02)
Irradiation of 4-allyloxy-2-quinolone and 4-(pent-4-enyloxy)-2-quinolone gave corresponding cross and parallel adducts specifically, whereas 4-(but-3-enyloxy)-2-quinolone led to a mixture of cross and parallel adducts.Regioselectivity in these photoreactions was not affected by the introduction of substituents into 4-(ω-alkenyloxy)-2-quinolones.These cross adducts were transformed to 2-substituted 1,2-dihydrocyclobutaquinolin-3(4H)-ones, whose synthesis could not be achived by using so-far known intermolecular photocycloaddition of 4-alkoxy-2-quinolone to olefins (the Kaneko-Naito method).Preliminary experiments demonstrated that these 2-substituted derivatives could be used as synthons for 7,8-disubstituted phenanthridin-6(5H)-ones by an application of the benzocyclobutene method.
